Herbicidal imidazolidine-2-one derivatives

ABSTRACT

An imidazolidine-2-one derivative represented by the formula ##STR1## wherein R 1  represents hydrogen atom, lower alkyl group, lower alkoxy lower alkyl group, benzyl group, lower alkoxycarbonyl lower alkyl group or lower alkylcarbamoyloxy group and R 2  represents a group --Ar or group --CONH--Ar wherein Ar represents a phenyl group, phenoxyphenyl group or aralkyloxyphenyl group each of which may be substituted with a halogen atom, nitro group, lower alkyl group, lower alkoxy group or haloalkyl group, a process for preparing the same and a herbicidal composition containing the same.

TECHNICAL FIELD AND DISCLOSURE OF INVENTION

This invention relates to novel imidazolidine-2-one derivatives, toprocesses for preparing the derivative and to herbicides containing thederivative as their active component.

The imidazolidine-2-one derivatives of the present invention are novelcompounds undisclosed in literature and represented by the formula [I].##STR2## wherein R¹ represents hydrogen atom, lower alkyl group, loweralkoxy lower alkyl group, benzyl group, lower alkoxycarbonyl lower alkylgroup or lower alkylcarbamoyloxy group and R² represents a group --Ar orgroup --CONH--Ar wherein Ar represents a phenyl group, phenoxyphenylgroup or aralkyloxyphenyl group each of which may be substituted with ahalogen atom, nitro group, lower alkyl group, lower alkoxy group orhaloalkyl group.

Particularly preferred compounds of the present invention represented bythe formula [I] are as follows:

compounds represented by the formula ##STR3## wherein R^(1') representshydrogen atom, lower alkyl group, lower alkoxy lower alkyl group, benzylgroup or lower alkoxycarbonyl lower alkyl group and Ar' represents aphenyl group, phenoxyphenyl group or aralkyloxyphenyl group each ofwhich may be substituted with a halogen atom, lower alkyl group, loweralkoxy group or haloalkyl group;

compounds represented by the formula ##STR4## wherein R^(1') is asdefined above and Ar" represents a phenyl group which may be substitutedwith a halogen atom, nitro group, lower alkyl group, lower alkoxy groupor haloalkyl group; and

compounds represented by the formula ##STR5## wherein R³ represents alower alkyl group, X' represents hydrogen atom, halogen atom, loweralkyl group, lower alkoxy group, benzyloxy group or haloalkyl group, andn is an integer of 1 to 3.

Exemplary of the lower alkyl groups mentioned in this specification aremethyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl,tert-butyl, etc. Representative of the lower alkoxy lower alkyl groupsare methoxymethyl, methoxyethyl, methoxypropyl, butoxymethyl, etc.Illustrative of the lower alkoxycarbonyl lower alkyl groups aremethoxycarbonylmethyl, ethoxycarbonylmethyl, propyloxycarbonylmethyl,methoxycarbonylethyl, ethoxycarbonylethyl, propyloxycarbonylethyl, etc.Examplary of the lower alkylcarbamoyloxy groups are methylcarbamoyloxy,ethylcarbamoyloxy, propylcarbamoyloxy, isopropylcarbamoyloxy, etc.Representative of the aralkyloxyphenyl groups are benzyloxyphenyl,phenethyloxyphenyl, etc. Illustrative of the halogen atoms are fluorine,chlorine, bromine, iodine, etc. Exemplary of the lower alkoxy groups aremethoxy, ethoxy, n-propyloxy, isopropyloxy, n-butoxy, etc.Representative of the haloalkyl groups are monochloromethyl,monochloroethyl, monochloropropyl, dichloroethyl, monobromomethyl,monobromoethyl, monobromopropyl, monofluoromethyl, trifluoromethyl,trifluoroethyl, etc. Illustrative of the phenyl groups substituted withhalogen, nitro, lower alkyl, lower alkoxy or haloalkyl are2-chlorophenyl, 3-chlorophenyl, 3,4-dichlorophenyl, 2-fluorophenyl,2-nitrophenyl, 3-nitrophenyl, 2-methylphenyl, 3-methylphenyl,4-methylphenyl, 3,4-dimethylphenyl, 2-isopropylphenyl, 2-methoxyphenyl,3-methoxyphenyl, 2-n-propyloxyphenyl, 2-isopropyloxyphenyl,3-trifluoromethylphenyl, etc. Exemplary of the phenoxyphenyl groupssubstituted with halogen, nitro, lower alkyl, lower alkoxy or haloalkylare 2-chlorophenoxyphenyl, 3-chlorophenoxyphenyl, 2-nitrophenoxyphenyl,3-nitrophenoxyphenyl, 2-methylphenoxyphenyl, 4-methylphenoxyphenyl,3-trifluoromethylphenoxyphenyl, 2-methoxyphenoxyphenyl,4-methoxyphenoxyphenyl, etc. Representative of the aralkyloxyphenylgroups substituted with halogen, nitro, lower alkyl, lower alkoxy orhaloalkyl are 2-chlorobenzyloxyphenyl, 4-chlorobenzyloxyphenyl,2-nitrobenzyloxyphenyl, 4-methylbenzyloxyphenyl,2-methylbenzyloxyphenyl, 4-methoxybenzyloxyphenyl,3-trifluoromethylbenzyloxyphenyl, 2-chlorophenethyloxyphenyl,3-nitrophenethyloxyphenyl, 4-methylphenethyloxyphenyl,4-methoxyphenethyloxyphenyl, 3-trifluoromethylphenethyloxyphenyl, etc.

The compounds [I] of the present invention can be prepared by variousprocesses. Preferred examples of the process are carried out accordingto the following reaction equation. ##STR6## (In the reaction equations,R^(1") represents a lower alkyl group, lower alkoxy lower alkyl group,benzyl group or lower alkoxycarbonyl lower alkyl group, X represents ahalogen atom, R³ represents a lower alkyl group and R² is as definedabove.)

The hydantoin derivatives represented by the formula [II] or [III] whichare used as the starting material in the foregoing reaction equationsare compounds known heretofore. For example, the hydantoin derivativesof the formula [II] or [III] wherein R² is a group-CONH--Ar can beprepared from 1-methylhydantoin or 3-methylhydantoin and allylisocyanate by the conventional method. The reaction between the1-methylhydantoin and allyl isocyanate and the reaction between the3-methylhydantoin and allyl isocyanate are conducted under the sameconditions with or without a solvent. Useful solvents can be any ofsuitable solvents which do not adversely affect the reaction, such astoluene, xylene, chlorobenzene and like aromatic solvents. The ratiobetween the 1- or 3-methylhydantoin and the allyl isocyanate is notparticularly limited and can be suitably determined over a wide range.The amount of the latter is usually about 1 to about 10 moles,preferably about 1 to about 3 moles, per mole of the former. While thereaction temperature is not particularly limitative, the reactionadequately proceeds at about 100° to about 200° C. and is completedusually in about 3 to about 5 hours.

The reaction for reducing the compound [II] to the compound [Ia] and thereaction for reducing the compound [III] to the compound [Ib] can beeffected in an adequate solvent. Suitable examples of the solvent arewater, methyl alcohol, ethyl alcohol, propyl alcohol, butyl alcohol, andlike alcohols; and a mixture of at least one of such alcohols and atleast one of diethyl ether, dibutyl ether, tetrahydrofuran, dioxane andlike ethers. The reducing agents which can be used in the reaction forreducing the compound [II] or [III] to the compound [Ia] or [Ib]include, for example, sodium borohydride. The ratio between the compound[II] or [III] and the sodium borohydride is not particularly limited andcan be determined over a wide range. The latter is used in an amount ofusually about 0.1 to about 5 moles, preferably about 0.25 to about 1mole, per mole of the former. While the reaction temperature is notparticularly limited, the reation favorably proceeds at usually about-50° to about 100° C., preferably about 0° to about 50° C. and iscompleted in usually about 1 to about 5 hours.

The reaction between the compound [Ic] and the alkyl halide [IV] can beconducted in the absence of a solvent or in the presence of a suitablesolvent. The alkyl halides [IV] are compounds heretofore known. Adequateexamples of the solvent are water, methyl alcohol, ethyl alcohol, propylalcohol, butyl alcohol and like alcohols; diethyl ether, dipropyl ether,dibutyl ether, tetrahydrofuran, dioxane and like ethers; methylenechloride, chloroform and like halogenated hydrocarbons; benzene,toluene, xylene, chlorobenzene, nitrobenzene, and like aromaticsolvents; pyridine; ethyl acetate; acetonitrile; dimethylformamide; etc.The ratio between the compound [Ic] and the compound [IV] is notparticularly limited and can be selected from a broad range. The latteris used in an amount of usually about 1 to about 5 moles, preferablyabout 1 to about 2 moles, per mole of the former. The reaction of thecompound [Ic] with the compound [IV] involves the use of a base forcollecting the hydrogen halide produced as a by-product. Useful basesinclude, for example, sodium hydroxide, potassium hydroxide, sodiumcarbonate, potassium carbonate, triethylamine, tributylamine and liketertiary amines; pyridine; picoline, lutidine and like pyridines; sodiummetal; sodium hydride; sodium alkoxides; etc. The ratio between thecompound [Ic] and the agent for collecting the hydrogen halide is notparticularly limited and can be selected from a wide range. The latteris employed in an amount of usually about 1 to about 5 moles, preferablyabout 1 to about 2 moles, per mole of the former. Although the reactiontemperature is not particularly limited, the reaction favorably proceedsat usually about 0° to about 100° C. and is completed usually in about 5to about 10 hours.

The reaction between the compound [Ic] and the isocyanate compound [V]is carried out in the absence or presence of a solvent. The isocyanates[V] are compounds heretofore known. Suitable examples of the isocyanateare methyl isocyanate, ethyl isocyanate, n-propyl isocyanate, isopropylisocyanate, n-butyl isocyanate, isobutyl isocyanate, sec-butylisocyanate, etc. The reaction without a solvent is conducted desirablyin an autoclave under increased pressure to prevent the vaporization ofthe compound [V]. Solvents useful in the reaction can be any of suitablesolvents which do not adversely affect the reaction, such as diethylether, dipropyl ether, dibutyl ether, tetrahydrofuran, dioxane and likeethers; methylene chloride, chloroform and like halogenatedhydrocarbons; benzene, toluene, xylene, chlorobenzene and like aromaticsolvents; pyridine; acetonitrile; N,N-dimethylformamide; etc. The ratiobetween the compound [Ic] and the compound [V] is not particularlylimited and can be determined over a wide range. The latter is used inan amount of usually about 1 to about 5 moles, preferably about 1 toabout 2 moles, per mole of the former.

While the use of a catalyst is optional in carrying out the reactionbetween the compound [Ic] and the compound [V] in the absence of asolvent, it is preferred to use a catalyst in conducting the reaction ina solvent. Useful catalysts include, for example, tertiary amines suchas triethylamine, tributylamine, N,N-dimethylaniline,hexamethylenetetramine, etc. The catalyst is used in the usual amount,for example, generally in an amount of about 0.01 to about 0.5 mole permole of the compound [Ic]. The reaction temperature is not particularlylimited, but favorably proceeds at usually about 0° to about 150° C. andis completed in generally about 3 to about 15 hours.

The compound [I] of the present invention thus obtained is easilypurified by the usual method such as recrystallization, solventextraction, column chromatography or the like.

Examples of the present compounds which can be prepared by the foregoingmethods are: PG,13

1-methyl-3-phenyl-4-hydroxyimidazolidine-2-one;

1-methyl-3-(2-chlorophenyl)-4-hydroxyimidazolidine-2-one;

1-methyl-3-(3,4-dichlorophenyl)-4-hydroxyimidazolidine-2-one;

1-methyl-3-(3-methylphenyl)-4-hydroxyimidazolidine-2-one;

1-methyl-3-(4-methoxyphenyl)-4-hydroxyimidazolidine-2-one;

1-methyl-3-(4-benzyloxyphenyl)-4-hydroxyimidazolidine-2-one;

1-methyl-3-(4-phenoxyphenyl)-4-hydroxyimidazolidine-2-one;

1-methyl-3-(3,4-dichlrophenyl)-4-methoxyimidazoline-2-one;

1-methyl-3-(3,4-dichlorophenyl)-4-benzyloxyimidazolidine-2-one;

1-methyl-3-(3,4-dichlorophenyl)-4-ethoxycarbonylmethyloxyimidazolidine-2-one;

1-methyl-3-(3,4-dichlorophenyl)-4-methoxymethyloxyimidazolidine-2-one;

3-methyl-4-hydroxyimidazolidine-2-one-1-carboxyanilide;

3-methyl-5-hydroxyimidazolidine-2-one-1-carboxyanilide;

3-methyl-4-hydroxyimidazolidine-2-one-1-carboxy-(2'-chloroanilide);

3-methyl-5-hydroxyimidazolidine-2-one-1-carboxy-2'-chloroanilide);

3-methyl-4-hydroxyimidazolidine-2-one-1-carboxy-(3'-chloroanilide);

3-methyl-5-hydroxyimidazolidine-2-one-1-carboxy-(3'-chloroanilide);

3-methyl-5-hydroxyimidazolidine-2-one-1-carboxy-(2',4'-dichloroanilide);

3-methyl-4-hydroxyimidazolidine-2-one-1-carboxy-(3'-methylanilide);

3-methyl-5-hydroxyimidazolidine-2-one-1-carboxy-(3'-methylanilide);

3-methyl-5-hydroxyimidazolidine-2-one-1-carboxy-(2'-methoxyanilide);

3-methyl-5-hydroxyimidazolidine-2-one-1-carboxy-(3'-trifluoromethylanilide);

3-methyl-5-hydroxyimidazolidine-2-one-1-carboxy-(3'-nitroanilide);

3-methyl-4-methoxyimidazolidine-2-one-1-carboxyanilide;

3-methyl-5-ethoxyimidazolidine-2-one-1-carboxyanilide;

3-methyl-5-methoxyimidazolidine-2-one-1-carboxy-(2'-chloroanilide);

3-methyl-5-ethoxycarbonylmethylimidazolidine-2-one-1-carboxyanilide;

3-methyl-5-methoxymethoxyimidazolidine-2-one-1-carboxyanilide;

3-methyl-4-methylcarbamoyloxyimidazolidine-2-one-1-carboxylanilide;

3-methyl-4-ethylcarbamoyloxyimidazolidine-2-one-1-carboxyanilide;

3-methyl-4-isopropylcarbamoyloxyimidazolidine-2-one-1-carboxyanilide;

2',3-dimethyl-4-methylcarbamoyloxyimidazolidine-2-one-1-carboxyanilide;

3,3'-dimethyl-4-methylcarbamoyloxyimidazolidine-2-one-1-carboxyanilide;

2'-chloro-3-methyl-4-methylcarbamoyloxyimidazolidine-2-one-1-carboxyanilide;

2'-chloro-3-methyl-4-isopropylcarbamoyloxyimidazolidine-2-one-1-carboxyanilide;

2',4'-dichloro-3-methyl-4-methylcarbamoyloxyimidazlidine-2-one-1-carboxyanilide;

3'-chloro-3-methyl-4-methylcarbamoyloxyimidazolidine-2-one-1-carboxyanilide;

3-methyl-4'-methoxy-4-methylcarbamoyloxyimidazolidine-2-one-1-carboxyanilide;

3-methyl-4'-trifluoromethyl-4-methylcarbamoyloxyimidazolidine-2-one-1-carboxyanilide;and

3-methyl-4'-benzyloxy-4-methylcarbamoyloxyimidazolidine-2-one-1-carboxyanilide.

This invention also relates to herbicides containing as their activecomponent the imidazolidine-2-one derivative (I).

The compounds of the present invention are markedly effective incontrolling weeds such as Eclipta prostrata, Amaranthus retroflexus,Aeschynomeme indica, Alopecurus aequalis var. amurensis, PolygonumHydropiper, Artemisia princeps, Erigeron sumatrensis, Rumex japonicus,Lindernia pyxidaria, Rotela indica, Echinochloa Crus-galli, Digitariaadscendens Eleusine indica, Cyperus microiria, etc. Therefore, thepresent compounds are useful in preventing or controlling weeds whichare harmful to agricultural crop plants such as those of citrus, apples,soy beans, corns, mulberries, tea, paddyrice, etc. or which impair thesurrounding scenic beauty.

When used as a herbicide, the compounds of the present invention can beused singly or in admixture with adjuvants commonly used in manufactureof agricultural chemicals. The herbicidal composition containing thepresent compound can take any of forms among which an emulsion, wettablepowder and granules are suitable. Examples of useful adjuvants forachieving a stable and improved herbicidal effect are diatomaceousearth, kaolin, clay, bentonite, white carbon, talc and like extenders;polyoxyethylene alkyl ether, polyoxyethylene alkylphenyl ether,polyoxyethylene sorbitan fatty acid ester, polyoxyethylene fatty acidester, sodium alkyl benzensulfonate, sodium lignin sulfonate, sodiumalkylsulfate, sodium polyoxyethylene alkylsulfate and like nonionic oranionic surfactants; xylol, acetone, methanol, ethanol, isopropanol,dioxane, dimethylform amide, dimethyl sulfoxide, carbon tetrachlorideand like organic solvents; etc.

In formulating a herbicidal composition according to the presentinvention, adjuvants are used in such amount that about 1 to about 90%by weight, preferably about 5 to about 70% by weight, of the activecomponent is present in the composition. While an adequate amount of theherbicidal composition to be applied is variable with the form of thecomposition, application mode, application season, kind of weeds to becontrolled, particularly weather conditions and soil conditions tendingto affect the herbicidal effect, etc., and can be determined over a widerange, the herbicidal composition of the present invention is generallyapplied in an amount of about 5 to about 400 g/a, preferably about 10 toabout 100 g/a, calculated as the active component.

The present invention will be described below in more detail withreference to Reference Examples, Examples, Preparation Examples and TestExamples. The numbers of test compounds used in Test Examples correspondto the numbers of Examples.

REFERENCE EXAMPLE 1 Preparation of3-methylimidazolidine-2,4-dione-1-carboxyanilide

A 5.7 g (0.05 mole) quantity of 3-methylhydantion and 5.9 g of phenylisocyanate were dissolved in each other in an oil bath at 150° C. for 3hours. The solution was recrystallized from dimethylformamide, giving9.0 g of colorless crystals in 78% yield.

M.P.: 219° to 220° C.

The NMR data of the crystals analyzed in DMSO-d₆ were as follows.

δ 3.00 ppm (3H), δ 4.33 ppm (2H).

δ 7.00 ppm (5H).

    ______________________________________                                        Elementary analysis (for C.sub.11 H.sub.11 N.sub.3 O.sub.3)                            C           H      N                                                 ______________________________________                                        Found (%)  56.90         4.75   18.10                                         Calcd. (%) 56.89         4.77   18.09                                         ______________________________________                                    

The result thus obtained confirmed that the product thus prepared was acompound of the formula ##STR7##

REFERENCE EXAMPLE 2 Preparation of3-methylimidazolidine-2,5-dione-1-carboxyanilide

A 5.7 g (0.05 mole) quantity of 1-methylhydantoin and 5.9 g (0.05 mole)of phenyl isocyanate underwent dissolution in an oil bath at 180° C. for3 hours. The solution was washed well with water and recrystallized fromethanol, giving 3.7 g of colorless crystals in 32% yield.

M.P.: 160° to 160.5° C.

The NMR data of the crystals analyzed in DMSO-d₆ were as follows.

δ 3.03 ppm (3H), δ 4.00 ppm (2H).

δ 7.00-7.70 ppm (5H).

    ______________________________________                                        Elementary analysis (for C.sub.11 H.sub.11 N.sub.3 O.sub.3)                            C           H      N                                                 ______________________________________                                        Found (%)  56.91         4.76   18.07                                         Calcd. (%) 56.89         4.77   18.09                                         ______________________________________                                    

The above result confirmed that the product obtained above was acompound of the formula ##STR8##

EXAMPLE 1 Preparation of1-methyl-3-(3,4-dichlorophenyl)-4-hydroxyimidazolidine-2-one

A 10.4 g (0.04 mole) quantity of1-methyl-3-(3,4-dichlorophenyl)hydantoin was suspended in 80 ml ofmethanol. The suspension was cooled to 10° C. and 1.5 g of sodiumborohydride was added thereto with stirring. After the addition, themixture was stirred for 30 minutes and warmed to room temperature,followed by further agitation for 2 hours. After completion of thereaction, the reaction mixture was concentrated and water was added tothe residue to deposit crystals. The crystals were filtered andrecrystallized from ethanol, affording 9.2 g of white crystals in 88%yield.

M.P.: 185° to 186° C.

The NMR data of the crystals analyzed in DMSO-d₆ were as follows.

δ 2.85 ppm (3H), δ 3.28 ppm (1H).

δ 3.65 ppm (1H), δ 5.57 ppm (1H).

δ 6.45 ppm (1H), δ 7.36 ppm (1H).

δ 7.68 ppm (1H), δ 7.97 ppm (1H).

    ______________________________________                                        Elementary analysis (for C.sub.10 H.sub.10 N.sub.2 O.sub.2 Cl.sub.2)                   C           H      N                                                 ______________________________________                                        Found (%)  46.04         3.77   10.69                                         Calcd. (%) 46.00         3.86   10.73                                         ______________________________________                                    

The above result confirmed that the product obtained above was acompound of the formula ##STR9##

EXAMPLE 2 Preparation of1-methyl-3-(3,4-dichlorophenyl)-4-ethoxyimidazolidine-2-one

Dissolved in 100 ml of dimethylformamide was 10.4 g (0.04 mole) of1-methyl-3-(3,4-dichlorophenyl)-4-hydroxyimidazolidine-2-one. Thesolution was cooled to 10° C. and 2 g (0.04 mole) of sodium hydride wasadded to the solution with stirring. After the addition, the mixture wasstirred for 30 minutes and 4.4 g of ethyl bromide was added dropwise.The mixture was stirred at room temperature for 2 hours and water wasadded to the reaction mixture. The mixture was extracted with chloroformand the chloroform extract was concentrated, giving 9.5 g of an oil in82.1% yield.

The oil was purified by silica gel column chloromatography using as asolvent a mixture of benzene and ethyl acetate (1:1).

The oil was subjected to NMR in deuteriochloroform (CDCl₃) with thefollowing result.

δ 1.19 ppm (3H), δ 2.90 ppm (3H).

δ 3.30-3.72 ppm (4H).

δ 5.43 ppm (1H), δ 7.38 ppm (1H).

δ 7.60 ppm (1H), δ 7.90 ppm (1H).

    ______________________________________                                        Elementary analysis (for C.sub.12 H.sub.14 N.sub.2 O.sub.2 Cl.sub.2)                   C           H      N                                                 ______________________________________                                        Found (%)  49.79         4.81   9.72                                          Calcd. (%) 49.84         4.88   9.69                                          ______________________________________                                    

The above result confirmed that the product obtained above was acompound of the formula ##STR10##

EXAMPLES 3 TO 16

The same procedure as Example 1 or 2 was repeated to produce compounds.Table 1 below shows the melting points and NMR data of the compoundsthus obtained.

                                      TABLE 1                                     __________________________________________________________________________    Ex.                           M.P. NMR (δ, CDCl.sub.3 or                No.                                                                              Formula                    (°C.)                                                                       CDCl.sub.3 /DMSO-d.sub.6)                  __________________________________________________________________________        ##STR11##                 174-175                                                                            2.86 (3H), 3.25 (1H) 3.67 (1H), 5.56                                          (1H) 6.33 (1H), 7.28 (2H) 7.63 (2H)        4                                                                                 ##STR12##                 149-150                                                                            2.90 (3H), 3.28 (1H) 3.70 (1H), 5.63                                          (1H) 6.50 (1H), 7.20- 8.20 (4H)            5                                                                                 ##STR13##                 148-149                                                                            2.85 (3H), 3.25 (1H) 3.63 (1H), 3.78                                          (3H) 5.58 (1H), 6.32 (1H) 6.65 (1H),                                          7.20-  7.50 (3H)                           6                                                                                 ##STR14##                 165-167                                                                            2.82 (3H), 3.22 (1H) 3.60 (1H), 3.77                                          (3H) 5.48 (1H), 6.30 (1H) 6.88 (2H),                                          7.52 (2H)                                  7                                                                                 ##STR15##                 104-105                                                                            2.30 (3H), 2.60 (3H) 3.20 (1H), 3.52                                          (1H) 5.00 (1H), 5.41 (1H) 6.80-7.60                                           (4H)                                       8                                                                                 ##STR16##                 173-174                                                                            2.86 (3H), 3.25 (1H) 3.65 (1H), 5.60                                          (1H) 6.25 (1H), 7.0- 7.80 (5H)             9                                                                                 ##STR17##                 130-132                                                                            2.65 (3H), 3.05 (2H) 3.20 (1H), 3.55                                          (1H) 4.17 (2H), 4.95 (1H) 5.50 (1H),                                          6.95 (2H) 7.20-7.50 (7H)                   10                                                                                ##STR18##                 162-163                                                                            2.60 (3H), 3.17 (1H) 3.53 (1H), 4.65                                          (1H) 5.02 (2H), 5.40 (1H) 6.93 (2H),                                          7.40 (5H) 7.55 (2H)                        11                                                                                ##STR19##                 188-190                                                                            2.90 (3H), 3.30 (1H) 3.68 (1H), 5.60                                          (1H) 6.32 (1H), 6.90- 7.80 (9H)            12                                                                                ##STR20##                 150-151                                                                            2.68 (3H), 3.25 (1H)  3.60 (1H), 4.90                                         (1H) 5.50 (1H), 6.95 (4H) 7.32 (2H),                                          7.67 (2H)                                  13                                                                                ##STR21##                 133-134                                                                            2.90 (3H), 3.23 (3H) 3.50 (2H), 5.47                                          (1H) 7.40 (1H), 7.60 (1H) 7.90 (1H)        14                                                                                ##STR22##                 86-87                                                                              2.90 (3H), 3.35 (3H) 3.60 (2H), 4.72                                          (2H) 5.60 (1H), 7.40 (1H) 7.60 (1H),                                          7.80 (1H)                                  15                                                                                ##STR23##                 101-102                                                                            2.90 (3H), 3.50 (2H) 4.47 (2H), 5.57                                          (1H) 7.30-7.70 (7H) 7.88 (1H)              16                                                                                ##STR24##                 91-92                                                                              1.25 (3H), 2.90 (3H) 3.60 (2H), 4.08                                          (2H) 4.20 (2H), 5.65 (1H) 7.40 (1H),                                          7.63 (1H) 7.93 (1H)                        __________________________________________________________________________

EXAMPLE 17 Preparation of3-methyl-4-hydroxyimidazolidine-2-one-1-carboxyanilide

A 7.0 g (0.03 mole) quantity of3-methylimidazolidine-2,4-dione-1-carboxyanilide was suspended in 50 mlof methanol. The suspension was cooled to 10° C. and 1.2 g of sodiumborohydride was added with stirring. The mixture was stirred for 30minutes and warmed to room temperature, followed by further agitationfor 10 hours. After completion of the reaction, the reaction mixture wasconcentrated and water was added to the residue to deposit crystals. Thecrystals were filtered and recrystallized from ethanol, giving 5.4 g ofcolorless crystals in 76% yield.

M.P.: 156° to 157° C.

The NMR data of the crystals analyzed in deuteriochloroform were asfollows.

δ 2.70 ppm (3H), δ 3.85 ppm (2H).

δ 5.00 ppm (1H), δ 7.00-7.70 ppm (5H).

    ______________________________________                                        Elementary analysis (for C.sub.11 H.sub.13 N.sub.3 O.sub.3)                            C           H      N                                                 ______________________________________                                        Found (%)  56.13         5.59   17.87                                         Calcd. (%) 56.16         5.57   17.86                                         ______________________________________                                    

The above result confirmed that the product obtained above was acompound of the formula ##STR25##

EXAMPLE 18

The NMR data of the product analyzed in deuteriochloroform were asfollows.

δ 2.90 ppm (3H), δ 3.30 ppm (1H).

δ 3.65 ppm (1H), δ 4.47 ppm (1H).

δ 6.00 ppm (1H), δ 7.10-7.70 ppm (5H).

    ______________________________________                                        Elementary analysis (for C.sub.11 H.sub.13 N.sub.3 O.sub.3)                            C           H      N                                                 ______________________________________                                        Found (%)  56.18         5.54   17.89                                         Calcd. (%) 56.16         5.57   17.86                                         ______________________________________                                    

The above result confirmed that the product obtained above was acompound of the formula ##STR26##

EXAMPLE 19 Preparation of3-methyl-5-methoxyimidazolidine-2-one-1-carboxy-(3-methylanilide)

A 2.5 g (0.01 mole) of3-methyl-5-hydroxyimidazolidine-2-one-1-carboxy-(3-methylanilide) wasdissolved in 40 ml of dimethylformamide. The solution was cooled to 10°C. and 0.5 g (0.01 mole) of sodium hydride was added to the solutionwith stirring. The mixture was stirred for 30 minutes and 1.5 g (0.01mole) of methyl iodide was added dropwise. The mixture was stirred atroom temperature for 2 hours. Water was added to the reaction mixture todeposit crystals. The crystals were filtered and recrystallized fromethanol, giving 2.0 g of colorless crystals in 76% yield.

M.P.: 104° to 105° C.

The NMR data of the crystals analyzed in deuteriochloroform were asfollows.

δ 2.32 ppm (3H), δ 2.90 ppm (3H).

δ 3.24 ppm (1H), δ 3.52 ppm (3H).

δ 3.60 ppm (1H), δ 5.65 ppm (1H).

δ 6.97 ppm (1H), δ 7.20-7.50 ppm (3H).

    ______________________________________                                        Elementary analysis (for C.sub.13 H.sub.17 N.sub.3 O.sub.3)                            C           H      N                                                 ______________________________________                                        Found (%)  59.28         6.54   15.98                                         Calcd. (%) 59.30         6.51   15.96                                         ______________________________________                                    

The above result confirmed that the product thus obtained was a compoundof the formula ##STR27##

EXAMPLES 20 TO 34

Compounds were prepared in the same manner as in Examples 17 to 19.Table 2 below shows the melting points and NMR data of the compounds.

                                      TABLE 2                                     __________________________________________________________________________    Ex. No.                                                                            Formula                M.P. (°C.)                                                                     NMR (δ, CDCl.sub.3)                 __________________________________________________________________________    20                                                                                  ##STR28##             179-180 2.88 (3H), 2.90 (2H) 2.97 (1H), 5.10                                          (1H) 6.95-7.50 (3H) 8.25 (1H)             21                                                                                  ##STR29##             169-170 2.30 (3H), 2.70 (3H) 3.80 (2H), 4.50                                          (1H) 4.95 (1H), 6.95 (1H) 7.25 (3H)       22                                                                                  ##STR30##             168-169 2.93 (3H), 3.31 (1H) 3.70 (1H), 5.10                                          (1H) 6.00 (1H), 6.90- 7.65 (3H), 8.45                                         (1H)                                      23                                                                                  ##STR31##             160.5-161                                                                             2.93 (3H), 3.30 (1H) 3.44 (1H), 4.35                                          (1H) 6.00 (1H), 7.05- 7.50 (3H), 7.72                                         (1H)                                      24                                                                                  ##STR32##               201-201.5                                                                           2.90 (3H), 3.27 (1H) 3.70 (1H), 5.90                                          (1H) 6.45 (1H), 7.40 (2H) 7.90 (1H)       25                                                                                  ##STR33##             148-149 2.92 (3H), 3.30 (1H) 3.65 (1H), 4.70                                          (1H) 6.00 (1H), 6.90- 7.70 (3H), 8.30                                         (1H)                                      26                                                                                  ##STR34##             173-174 2.32 (3H), 2.90 (3H) 3.30 (1H), 3.65                                          (1H) 4.47 (1H), 6.00 (1H) 7.05-7.45                                           (3H) 8.05 (1H)                            27                                                                                  ##STR35##               164-164.5                                                                           2.32 (3H), 2.90 (3H) 3.27 (1H), 3.60                                          (1H) 4.63 (1H), 6.00 (1H) 7.00 (1H),                                          7.35 (3H)                                 28                                                                                  ##STR36##             196-197 2.30 (3H), 2.90 (3H) 3.23 (1H), 3.60                                          (1H) 6.95 (2H), 7.12 (2H) 7.45 (2H)       29                                                                                  ##STR37##             174-175 2.85 (3H), 3.20 (1H) 3.55 (1H), 3.82                                          (3H) 4.50 (1H), 5.85 (1H) 6.80-7.10                                           (3H) 8.10 (1H)                            30                                                                                  ##STR38##             154-155 2.90 (3H), 3.26 (1H) 3.60 (1H), 3.80                                          (3H) 4.63 (1H), 5.96 (1H) 6.70 (1H),                                          7.05- 7.40 (3H)                           31                                                                                  ##STR39##             75-76   2.31 (3H), 2.90 (3H) 2.30 (1H), 2.40                                          (3H) 3.61 (1H), 4.68 (1H) 5.18 (1H),                                          5.82 (1H) 6.80-7.50 (1H)                  32                                                                                  ##STR40##             127-128 1.25 (3H), 2.32 (3H) 2.91 (3H), 3.65                                          (2H) 4.21 (2H), 4.56 (2H) 5.77 (1H),                                          6.90- 7.50 (4H)                           33                                                                                  ##STR41##             162-164 2.86 (3H), 3.34 (1H) 3.70 (1H), 5.15                                          (1H) 6.00 (1H), 6.5- 7.5 (4H)             34                                                                                  ##STR42##             146-148 2.90 (3H), 3.20 (1H) 3.64 (1H), 4.63                                          (1H) 5.85 (1H), 6.9- 7.5                  __________________________________________________________________________                                        (4H)                                  

EXAMPLE 35 Preparation of3.3'-dimethyl-4-hydroxyimidazolidine-2-one-1-carboxyanilide

A 7.4 g (0.03 mole) quantity of3.3'-dimethylimidazolidine-2,5-dione-1-carboxyanilide was suspended in50 ml of methanol. The suspension was cooled to 10° C. and 1.2 g (0.03mole) of sodium boron hydride was added with stirring. The mixture wasagitated for 30 minutes and was warmed to room temperature, followed byfurther agitation for 2 hours. After completion of the reaction, thereaction mixture was concentrated and water was added to the residue todeposit crystals. The crystals were filtered and recrystallized fromethanol, giving 6.7 g of colorless crystals in 90% yield.

M.P.: 164° to 164.5° C.

EXAMPLE 36 Preparation of3.3'-dimethyl-4-methylcarbamoyloxyimidazolidine-2-one-1-carboxyanilide

Dissolved in 50 ml of chloroform was 5.0 g (0.02 mole) of3.3'-dimethyl-4-hydroxyimidazolidine-2-one-1-carboxyanilide.Triethylamine (0.5 ml) was added to the solution. The mixture was cooledto 5° C. and 1.7 g (0.03 mole) of methyl isocyanate was added dropwisewith stirring. Further stirring continued for 30 minutes and thereaction mixture was warmed to room temperature, followed by 5 hours ofagitation. After completion of the reaction, the reaction mixture wasconcentrated under reduced pressure to afford a crystalline residue. Theresidue was recrystallized from ethanol, giving 5.2 g of colorlesscrystals in 85% yield.

M.P.: 130° to 131° C.

The NMR data of the crystals analyzed in deuteriochloroform were asfollows.

δ 2.30 ppm (3H), δ 2.77 ppm (3H).

δ 2.80 ppm (3H), δ 3.30 ppm (1H).

δ 5.17 ppm (1H), δ 6.75 ppm (1H).

δ 6.80-7.50 ppm (4H).

    ______________________________________                                        Elementary analysis (for C.sub.14 H.sub.18 N.sub.4 O.sub.4 = 306.32)                   C           H      N                                                 ______________________________________                                        Found (%)  54.85         5.93   18.31                                         Calcd. (%) 54.89         5.92   18.29                                         ______________________________________                                    

The above result confirmed that the product obtained above was acompound of the formula ##STR43##

EXAMPLE 37 Preparation of4'-chloro-3-methyl-4-ethylcarbamoyloxyimidazolidine-2-one-1-carboxyanilide

Dissolved in 40 ml of chloroform was 2.7 g (0.01 mole) of4'-chloro-3-methyl-4-hydroxyimidazolidine-2-one-1-carboxyanilide. To thesolution was added 0.4 ml of triethylamine. The mixture was cooled to 5°C. and 1.1 g (0.015 mole) of ethyl isocyanate was added dropwise withstirring. Further agitation followed for 30 minutes and the reactionmixture was warmed to room temperature, followed by 12 hours ofagitation. After completion of the reaction, the reaction mixture wasconcentrated under reduced pressure to afford a crystalline residue. Theresidue was recrystallized from ethanol, giving 2.6 g of colorlesscrystals in 77% yield.

M.P.: 156° to 157° C.

The NMR data of the crystals analyzed in deuteriochloroform were asfollows.

δ 1.12 ppm (3H), δ 2.82 ppm (3H).

δ 3.10-3.50 ppm (3H).

δ 3.70 ppm (1H), δ 5.20 ppm (1H).

δ 6.70 ppm (1H), δ 7.28 ppm (2H).

7.53 ppm (2H).

    ______________________________________                                        Elementary analysis (for C.sub.14 H.sub.17 N.sub.4 O.sub.4 Cl = 340.77)                C           H      N                                                 ______________________________________                                        Found (%)  49.30         5.05   16.45                                         Calcd. (%) 49.35         5.03   16.44                                         ______________________________________                                    

The above result confirmed that the product obtained above was acompound of the formula ##STR44##

EXAMPLES 38 TO 52

The same procedure as Example 36 or 37 was repeated to producecompounds. Table 3 below shows the melting points and NMR data of thecompounds obtained.

                                      TABLE 3                                     __________________________________________________________________________    Ex. No.                                                                            Formula                 M.P. (°C.)                                                                   NMR (δ, CDCl.sub.3)                  __________________________________________________________________________    38                                                                                  ##STR45##              150-151                                                                             2.82 (3H), 2.85 (3H) 3.35 (1H), 3.72                                          (1H) 5.20 (1H), 6.78 (1H) 7.10-7.70                                           (5H)                                       39                                                                                  ##STR46##              163-164                                                                             2.76 (3H), 2.85 (3H) 3.30 (1H), 3.70                                          (1H) 5.20 (1H), 6.63 (1H) 6.81-7.40                                           (3H) 8.20 (1H)                             40                                                                                  ##STR47##              184-185                                                                             2.79 (3H), 2.83 (3H) 3.30 (1H), 3.72                                          (1H) 5.15 (1H), 6.73 (1H) 7.29 (2H),                                          7.55 (2H)                                  41                                                                                  ##STR48##              164-165                                                                             2.33 (3H), 2.63 (3H) 2.78 (3H), 3.22                                          (1H) 3.65 (1H), 5.60 (1H) 6.75 (1H),                                          7.00- 7.30 (3H), 8.12 (1H)                 42                                                                                  ##STR49##              172-173                                                                             2.80 (6H), 3.35 (1H) 3.72 (1H), 5.20                                          (1H) 6.75 (1H), 7.30- 7.70 (3H), 8.00                                         (1H)                                       43                                                                                  ##STR50##              138-139                                                                             2.75 (3H), 2.86 (3H) 3.35 (1H), 3.70                                          (1H) 5.00 (1H), 5.20 (1H) 6.75 (1H),                                          6.90- 7.10 (3H), 7.25- 7.60 (5H), 8.32                                        (1H)                                       44                                                                                  ##STR51##              130-131                                                                             1.40 (6H), 2.82 (3H) 2.90 (3H), 3.15-                                         3.50 (2H), 3.72 (1H) 4.70 (1H), 6.75                                          (1H) 6.90-7.20 (3H) 8.30 (1H)              45                                                                                  ##STR52##              138-139                                                                             1.12 (3H), 2.82 (3H) 3.10-3.50 (3H)                                           3.70 (1H), 5.15 (1H) 6.73 (1H), 7.10-                                         7.70 (5H)                                  46                                                                                  ##STR53##              154-155                                                                             1.13 (3H), 2.29 (6H) 2.73 (3H), 3.05-                                         3.45 (3H), 3.70 (1H) 5.35 (1H), 6.60-                                         7.20 (3H), 7.97 (1H)                       47                                                                                  ##STR54##              161-162                                                                             1.12 (3H), 2.80 (3H) 3.23 (2H), 3.30                                          (1H) 3.68 (1H), 3.79 (3H) 5.40 (1H),                                          6.72 (1H) 6.89 (2H), 7.49 (2H)             48                                                                                  ##STR55##              137-138                                                                             0.90 (3H), 1.45 (2H) 2.85 (3H), 3.15                                          (2H) 3.36 (1H), 3.72 (1H) 5.20 (1H),                                          6.73 (1H) 7.28 (2H), 7.55 (2H)             49                                                                                  ##STR56##              139-140                                                                             0.93 (3H), 1.50 (2H) 2.30 (6H), 2.80                                          (3H) 3.20 (2H), 3.35 (1H) 3.72 (1H),                                          5.28 (1H) 6.75 (1H), 6.80- 7.18 (2H),                                         8.00 (1H)                                  50                                                                                  ##STR57##              170-171                                                                             1.15 (6H), 2.86 (3H) 3.45 (1H), 3.55-                                         4.00 (2H), 4.95 (1H) 6.70 (1H), 7.10-                                         7.70 (5H)                                  51                                                                                  ##STR58##              196-197                                                                             1.15 (6H), 2.32 (3H) 2.78 (3H), 3.32                                          (1H) 3.55-3.90 (2H) 5.10 (1H), 6.70                                           (1H) 7.00-7.35 (3H) 8.10 (1H)              52                                                                                  ##STR59##              156-157                                                                             1.15 (6H), 2.30 (3H) 2.76 (3H), 3.25                                          (1H) 3.50-4.00 (2H) 5.25 (1H), 6.69                                           (1H) 6.95 (1H), 7.15-7.50                  __________________________________________________________________________                                       (3H)                                   

    ______________________________________                                        Preparation Example 1 (50% wettable powder)                                                      Part by weight                                             ______________________________________                                        Compound obtained in Example 1                                                                     50                                                       Sodium lignin sulfonate                                                                             1                                                       Sodium dodecylbenzenesulfonate                                                                      4                                                       Clay                 45                                                       ______________________________________                                    

    ______________________________________                                        Preparation Example 2 (30% emulsion)                                                             Part by weight                                             ______________________________________                                        Compound obtained in Example 2                                                                     30                                                       Polyoxyethylenenonyl phenyl ether                                                                  10                                                       Dimethylformamide    20                                                       Xylene               40                                                       ______________________________________                                    

    ______________________________________                                        Preparation Example 3 (10% granules)                                                             Part by weight                                             ______________________________________                                        Compound obtained in Example 3                                                                     10                                                       Sodium lignin sulfonate                                                                            0.5                                                      Sodium dodecylbenzenesulfonate                                                                     2                                                        Diatomaceous earth   27.5                                                     Bentonite            60                                                       ______________________________________                                    

The wettable powder was prepared by pulverizing a uniform admixture ofthe components. The emulsion was produced by dissolving a uniformadmixture of the components. The granules were prepared by adding waterto a uniform admixture of the components, fully kneading the mixture,granulating the resulting mass, finely dividing the granules and dryingthe finely divided particles.

TEST EXAMPLE 1 (test by application of the herbicide to soil)

Wagner pots each having an area of 1/2000 a were filled with sterilizedalluvial soil. Then the pots were each planted with seeds of plants inTable 4 below which were subsequently covered with soil about 0.5 toabout 1.0 cm deep. Wettable powders each containing as the activecomponent the compound obtained in respective Examples were preparedaccording to Preparation Example 1 and applied after dilution with waterin an amount of 100 g/a calculated as the active component in suchmanner as to uniformly wet the entire surface of soil. The herbicidalactivity of each sample was observed with unaided eye and evaluated 3weeks after the application thereof according to the criteria indicatedbelow in which the herbicidal activity thereof is expressed in terms ofan index compared with untreated plants. Table 4 below shows theresults.

    ______________________________________                                        Index       Herbicidal Activity                                               ______________________________________                                        0           No change                                                         1            1-24%*                                                           2           25-49%                                                            3           50-74%                                                            4           75-90%                                                            5           Completely killed                                                 ______________________________________                                         *The percentages represent a degree of growth inhibition.                

                  TABLE 4                                                         ______________________________________                                        Test        Herbicidal activity                                               compound    A     B       C   D     E   F     G                               ______________________________________                                        1           5     5       5   5     5   5     5                               2           5     5       5   5     5   5     5                               3           5     5       5   5     5   5     5                               4           5     5       5   5     5   5     5                               5           5     4       3   3     5   4     3                               6           5     5       1   1     4   0     2                               7           5     5       5   5     5   5     5                               8           5     5       3   3     5   3     4                               13          5     5       5   5     5   5     5                               14          5     5       5   5     5   5     5                               15          5     5       5   5     5   4     5                               16          5     5       5   5     5   5     5                               18          5     5       5   5     5   5     5                               19          5     5       5   5     5   5     5                               20          5     5       4   1     5   4     1                               21          5     4       5   2     4   4     2                               22          5     5       5   5     5   5     5                               23          5     5       5   5     5   5     5                               24          4     5       4   5     5   3     1                               25          5     5       5   5     5   5     5                               26          5     5       5   5     5   5     5                               27          5     5       5   5     5   5     5                               28          5     5       5   2     4   1     3                               29          5     5       5   2     2   5     1                               30          5     5       5   5     5   5     5                               31          5     5       5   5     5   5     5                               32          5     5       5   5     5   5     5                               33          5     5       5   5     5   4     5                               34          5     5       5   5     5   5     5                               37          5     4       5   2     4   4     2                               38          5     5       5   5     5   5     5                               39          5     5       5   5     5   5     5                               40          4     5       4   5     5   3     1                               41          5     5       5   5     5   5     5                               42          5     5       5   5     5   5     5                               43          3     2       2   3     1   1     1                               44          5     5       5   5     5   5     5                               45          5     4       5   3     4   4     3                               46          5     5       5   2     4   1     3                               47          5     5       5   2     2   5     1                               48          5     4       5   2     4   4     2                               49          5     5       5   5     5   5     5                               50          5     5       5   5     5   5     5                               51          5     5       5   5     5   5     5                               52          5     5       5   5     5   5     5                               Control                                                                       compound A* 1     2       2   3     1   0     2                               compound B**                                                                              0     0       0   0     0   0     0                               ______________________________________                                         *Isocarbamide [N(2methylpropyl)-2-oxo-1-imidazolidine-carboxyamide] of th     formula                                                                       ##STR60##                                                                     **1-Methyl-4-hydroxyimidazolidine-2-one of the formula                        ##STR61##                                                                

The test plants A to G shows in Table 4 were as follows.

A: Amaranthus retroflexus

B: Aeschynomene indica

C: Echinochloa Crus-galli

D: Raphanus sativus

E: Fagopyrum esculentum

F: Pharbitis Nil var. japonica

G: Triticum

TEST EXAMPLE 2 (test by application to stems and leaves)

Wagner pots each having an area of 1/2000 a were filled with sterilizedalluvial soil. Then the pots were each planted with seeds of weeds shownin Table 4. When the weeds grew to a specific height (substantially tothe 2 or 3 leaf stage), emulsions each containing as the activeingredient respective compounds obtained in Examples were preparedaccording to Preparation Example 2 and applied after dilution with waterin an amount of 100 g/a calculated as the active component in suchmanner as to uniformly wet the entire surfaces of weed stems and leaves.The herbicidal activity of each sample was evaluated 3 weeks after theapplication thereof. Table 5 below shows the result. The criteria forevaluation were the same as in Test Example 1.

                  TABLE 5                                                         ______________________________________                                        Test     Herbicidal activity                                                  compound A      B      C    D    E    F    G    H                             ______________________________________                                         1       5      5      5    5    5    5    5    5                              2       5      5      4    5    5    5    2    3                              4       5      5      5    5    5    5    5    5                              9       5      1      0    5    5    5    2    3                             10       5      2      2    3    5    4    1    5                             11       5      2      2    4    5    5    1    4                             12       5      0      0    2    5    5    1    5                             13       3      5      2    2    5    3    2    2                             14       5      5      5    5    5    5    5    5                             15       4      1      1    2    5    5    2    3                             16       5      5      2    5    5    4    5    5                             17       3      5      4    5    5    5    1    5                             18       5      5      5    5    5    5    5    5                             19       5      5      5    5    5    5    5    5                             20       5      5      5    5    5    5    5    5                             21       5      5      5    5    5    5    5    5                             22       5      5      5    5    5    5    5    5                             23       5      5      5    5    5    5    5    5                             25       5      5      5    5    5    5    5    5                             26       5      5      5    5    5    5    5    5                             27       5      5      5    5    5    5    5    5                             30       5      5      5    5    5    5    5    5                             31       5      5      5    5    5    5    5    5                             32       5      5      5    5    5    5    5    5                             33       5      5      5    5    5    5    5    5                             34       5      5      5    5    5    5    5    5                             36       5      5      5    5    5    5    5    5                             37       5      5      5    5    5    5    4    4                             38       5      5      5    5    5    5    5    5                             39       5      5      5    5    5    5    5    5                             40       5      5      5    5    5    5    4    5                             41       5      5      5    5    5    5    5    5                             42       5      5      5    5    5    5    5    5                             43       4      4      4    5    5    3    4    3                             44       5      5      5    5    5    5    5    5                             46       5      5      5    5    5    5    4    4                             48       5      5      5    5    5    5    5    5                             50       5      5      5    5    5    5    5    5                             51       5      5      5    5    5    5    5    5                             52       5      5      5    5    5    5    5    5                             Control  1      5      2    2    3    2    0    2                             compound A                                                                    Control  0      0      0    0    0    0    0    0                             compound B                                                                    ______________________________________                                    

Control compounds A and B were the same as those indicated in Table 4.The test plants A to G were also the same as in Table 4. H conotesEclipta prostrata.

TEST EXAMPLE 3 (test by application of the herbicide to immersed plants)

Wagner pots each having an area of 1/5000 a were filled with soil forpaddy field. In the pot was placed a soil portion to provide an outerlayer which portion was mixed with seeds of Panicum crus-galli, Cyperusdifformis, Lindernia Pyxilaria and Rotala indica. var. uliginosa. Thetuber of Sagittaria pygmaea was planted in the pot which was thensupplied with water 3 cm deep. Granules were prepared according toPreparation Example 3. After planting paddy-rice plants, the herbicidesamples were applied in an amount of 50 g/a calculated as the activecomponent. Three weeks after the application of the samples, theherbicidal activity of the samples against the plants were evaluatedwith the result as indicated in Table 6 below. The evaluation wasconducted according to the same criteria as in Test Example 1.

                  TABLE 6                                                         ______________________________________                                        Test        Herbicidal activity                                               compound    I     J        C   K      L   M                                   ______________________________________                                         1          5     5        5   5      3   --                                   2          5     5        5   5      3   --                                   3          5     5        3   2      0   --                                   4          5     5        5   4      3   --                                   5          4     3        5   1      3   --                                   6          4     4        5   3      0   --                                   7          3     3        5   4      1   --                                   8          4     3        5   1      0   --                                   9          3     5        5   5      1   --                                  12          3     5        5   5      3   --                                  13          5     5        5   5      4   --                                  14          5     5        5   5      5   --                                  15          5     5        5   5      3   --                                  16          5     5        5   4      3   --                                  18          --    5        5   5      --  5                                   20          --    5        5   5      --  5                                   24          --    5        5   5      --  5                                   25          --    5        5   5      --  5                                   27          --    5        5   5      --  5                                   28          --    5        5   5      --  5                                   29          --    5        5   5      --  5                                   34          --    5        5   5      --  5                                   36          --    5        5   5      --  5                                   38          --    5        5   5      --  5                                   44          --    5        5   5      --  5                                   50          --    5        5   5      --  5                                   52          --    5        5   5      --  5                                   Control     --    3        3   2      --  2                                   compound A                                                                    Control     0     0        0   0      0   --                                  compound B                                                                    ______________________________________                                    

The control compounds A and B were the same as those in Table 4. Testplants C and I to M were as follows.

C: Echinochloa Grus-galli

I: Rotala indica

J: Lindernia Pyxidaria

K: Cyperus microiria

L: Sagittaria pygmaea

M: Cyperus difformis

I claim:
 1. An imidazolidine-2-one derivative represented by the formula##STR62## wherein R¹ represents hydrogen, lower alkyl, lower alkoxylower alkyl, benzyl, lower alkoxycarbonyl lower alkyl or loweralkylcarbamoyloxy and R² represents --Ar or --CONH--Ar wherein Arrepresents phenyl, phenoxyphenyl, benzyloxyphenyl or phenethyloxyphenyl,each of which may be substituted with a halogen atom, nitro group, loweralkyl group, lower alkoxy group or haloalkyl group of 1-3 carbons and upto 3 halogens.
 2. A compound as defined in claim 1 which is representedby the formula ##STR63## wherein R^(1') represents hydrogen, loweralkyl, lower alkoxy lower alkyl, benzyl or lower alkoxycarbonyl loweralkyl and Ar' represents phenyl, phenoxyphenyl, benzyloxyphenyl orphenethyloxyphenyl, each of which may be substituted with a halogenatom, lower alkyl group, lower alkoxy group or haloalkyl group of 1-3carbons and up to 3 halogens.
 3. A compound as defined in claim 1 whichis represented by the formula ##STR64## wherein R^(1') represents ahydrogen, lower alkyl, lower alkoxy lower alkyl, benzyl or loweralkoxycarbonyl lower alkyl and Ar" represents phenyl which may besubstituted with a halogen atom, nitro group, lower alkyl group, loweralkoxy group or haloalkyl group of 1-3 carbons and up to 3 halogens. 4.A compound as defined in claim 1 which is represented by the formula##STR65## wherein R³ represents lower alkyl, X' represents hydrogen,halogen, lower alkyl, lower alkoxy, benzyloxy or haloalkyl of 1-3carbons up to 3 halogens, and n is an integer of 1 to
 3. 5. A herbicidalcomposition containing a herbicidally effective amount of animidazolidine-2-one derivative represented by the formula ##STR66##wherein R¹ represents hydrogen, lower alkyl, lower alkoxy lower alkyl,benzyl, lower alkoxycarbonyl lower alkyl or lower alkylcarbamoyloxy andR² represents --Ar or --CONH--Ar wherein Ar represents phenyl,phenoxyphenyl, benzyloxyphenyl or phenethyloxyphenyl, each of which maybe substituted with a halogen atom, nitro group, lower alkyl group,lower alkoxy group or haloalkyl group of 1-3 carbons and up to 3halogens, in combination with a carrier therefor.
 6. A herbicidalcomposition as defined in claim 5, wherein the imidazolidine-2-onederivative is represented by the formula: ##STR67## wherein R¹represents hydrogen, lower alkyl, lower alkoxy lower alkyl, benzyl orlower alkoxycarbonyl lower alkyl and Ar' represents phenyl,phenoxyphenyl, benzyloxyphenyl or phenethyloxyphenyl, each of which maybe substituted with a halogen atom, lower alkyl group, lower alkoxygroup or haloalkyl group of 1-3 carbons and up to 3 halogens.
 7. Aherbicidal composition as defined in claim 5, wherein theimidazolidine-2-one derivative is represented by the formula: ##STR68##wherein R^(1') represents a hydrogen, lower alkyl, lower alkoxy loweralkyl, benzyl or lower alkoxycarbonyl lower alkyl and Ar" representsphenyl which may be substituted with a halogen atom, nitro group, loweralkyl group, lower alkoxy group or haloalkyl group of 1-3 carbons and upto 3 halogens.
 8. A herbicidal composition as defined in claim 5,wherein the imidazolidine-2-one derivative is represented by theformula: ##STR69## wherein R³ represents lower alkyl, X' representshydrogen, halogen, lower alkyl, lower alkoxy, benzyloxy or haloalkyl of1-3 carbons and up to 3 halogens, and n is an integer of 1 to
 3. 9. Amethod of controlling weeds comprising applying to the weeds aherbicidally effective amount of an imidazolidine-2-one derivativerepresented by the formula: ##STR70## wherein R¹ represents hydrogen,lower alkyl, lower alkoxy lower alkyl, benzyl, lower alkoxycarbonyllower alkyl or lower alkylcarbamoyloxy and R² represents --Ar or--CONH--Ar wherein Ar represents phenyl, phenoxyphenyl, benzyloxyphenylor phenethyloxyphenyl, each of which may be substituted with a halogenatom, nitro group, lower alkyl group, lower alkoxy group or haloalkylgroup of 1-3 carbons and up to 3 halogens.
 10. A method of controllingweeds as defined in claim 9, wherein the imidazolidine-2-one derivativeis represented by the formula: ##STR71## wherein R^(1') representshydrogen, lower alkyl, lower alkoxy lower alkyl, benzyl or loweralkoxycarbonyl lower alkyl and Ar' represents phenyl, phenoxyphenyl,benzyloxyphenyl or phenethyloxyphenyl, each of which may be substitutedwith a halogen atom, lower alkyl group, lower alkoxy group or haloalkylgroup of 1-3 carbons and up to 3 halogens.
 11. A method of controllingweeds as defined in claim 9, wherein the imidazolidine-2-one derivativeis represented by the formula: ##STR72## wherein R^(1') represents ahydrogen, lower alkyl, lower alkoxy lower alkyl, benzyl or loweralkoxycarbonyl lower alkyl and Ar" represents phenyl which may besubstituted with a halogen atom, nitro group, lower alkyl group, loweralkoxy group or haloalkyl group of 1-3 carbons and up to 3 halogens. 12.A method of controlling weeds as defined in claim 9, wherein theimidazolidine-2-one derivative is represented by the formula: ##STR73##wherein R³ represents lower alkyl, X' represents hydrogen, halogen,lower alkyl, lower alkoxy, benzyloxy or haloalkyl of 1-3 carbons and upto 3 halogens, and n is an integer of 1 to 3.